Proscaline

Proscaline
Clinical data
Other names	4-Propoxy-3,5-dimethoxyphenethylamine; 4-Propoxy-3,5-DMPEA
Routes of; administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Duration of action	8–12 hours
Identifiers
	IUPAC name 2-(3,5-dimethoxy-4-propoxyphenyl)ethan-1-amine;
CAS Number	39201-78-0 [EPA];
PubChem CID	15102790;
ChemSpider	10439596 ;
UNII	99G781N5IO;
ChEMBL	ChEMBL340765 ;
CompTox Dashboard (EPA)	DTXSID00192454 ;
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(cc(OC)c1OCCC)CCN;
	InChI InChI=1S/C13H21NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h8-9H,4-7,14H2,1-3H3 ; Key:HYWLMSUAZVDUFW-UHFFFAOYSA-N ;
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Proscaline, also known as 4-propoxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families.^[1] It has structural properties similar to the drugs mescaline, isoproscaline, and escaline.^[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin reports that a dose of 30 to 60 mg produces effects lasting 8 to 12 hours.^[1]^[2]

Interactions

Pharmacology

Pharmacodynamics

Proscaline is a serotonin 5-HT₂ receptor agonist.^[3] This is thought to be responsible for its psychedelic effects.^[3]

Chemistry

Proscaline is in a class of compounds commonly known as phenethylaines, and is the 4-propoxy homologue of mescaline. The full name of the chemical is 4-propoxy-3,5-dimethoxyphenethylamine.

Society and culture

Legal status

United Kingdom

Proscaline is a Class A controlled substance in the UK.

United States

Proscaline is not directly scheduled under the Controlled Substances Act. However, due to its structural similarities with mescaline, a Schedule I drug, it could potentially be subject to the same control measures and penalties for possession and manufacture under the Federal Analogue Act.

References

^ ^a ^b ^c ^d ^e Proscaline entry in PiHKAL
^ Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Table 4 Human potency data for selected hallucinogens. [...]
^ ^a ^b Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.

[PiHKAL-1] Proscaline entry in PiHKAL

[HalberstadtChathaKlein2020-2] Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Table 4 Human potency data for selected hallucinogens. [...]

[WallachCaoCalkins2023-3] Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.

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